Efficient synthesis of 2-amino-4-aryl-8-[(E)-arylmethylidene]-5, 6, 7, 8-4H pyrano [3, 2-c]pyridine in green media

被引：4

作者：

Balalaie, Saeed ^{[1
]}

Mehrazar, Mehrdad ^{[1
]}

Haghighatnia, Yaghoub ^{[1
]}

机构：

[1] KN Toosi Univ Technol, Peptide Chem Res Ctr, Tehran, Iran

来源：

GREEN CHEMISTRY LETTERS AND REVIEWS | 2013年 / 6卷 / 01期

关键词：

tetrahydro-4H-pyrano [3; 2-c]pyridine-3-carbonitriles; green media; diammonium hydrogen phosphate; piperidine; ring closure; atom-economy; condensation reaction; DIAMMONIUM HYDROGEN PHOSPHATE; ONE-POT SYNTHESIS; DIELS-ALDER REACTION; ORGANIC-REACTIONS; AQUEOUS-MEDIA; SOLVENT-FREE; WATER; DERIVATIVES; CYCLOADDITION; VERSATILE;

D O I：

10.1080/17518253.2012.709280

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient, general, and atom-economic procedure for the synthesis of 2-amino-6 methyl-4-aryl-8-[(E)-arylmethylidene]-5, 6, 7, 8-4H-pyrano [3, 2-c]pyridine-3-carbonitriles has been developed by reaction of 3,5-bis[(E)-arylmethylidene]-tetrahydro-4(1H)-pyridinones with malononitrile. The reaction proceeds under green media (EtOH/H2O, 1:1) and in the presence of diammonium hydrogen phosphate (10%) or piperidine (10%) to afford pyranopyridines at room temperature with good high yields. [GRAPHICS] .

引用

页码：101 / 105

页数：5

共 44 条

[1] Novel and efficient catalysts for the one-pot synthesis of 3,4-dihydropyrano[c]chromene derivatives in aqueous media
Abdolmohammadi, Shahrzad
Balalaie, Saeed
[J]. TETRAHEDRON LETTERS, 2007, 48 (18) : 3299 - 3303
[2] An efficient green chemical approach for the synthesis of structurally diverse spiroheterocycles with fused heterosystems
Arya, Anand Kumar
Kumar, Mahendra
[J]. GREEN CHEMISTRY, 2011, 13 (05) : 1332 - 1338
[3] Diammonium hydrogen phosphate as a versatile and efficient catalyst for the one-pot synthesis of pyrano[2,3-d]pyrimidinone derivatives in aqueous media
Balalaie, Saeed
Abdolmohammadi, Shahrzad
Bijanzadeh, Hamid Reza
Amani, Ali Mohammad
[J]. MOLECULAR DIVERSITY, 2008, 12 (02) : 85 - 91
[4] Diammonium hydrogen phosphate:: An efficient and versatile catalyst for the one-pot synthesis of tetrahydrobenzo[b]pyran derivatives in aqueous media
Balalaie, Saeed
Bararjanian, Morteza
Sheikh-Ahmadi, Masoumeh
Hekmat, Shohreh
Salehi, Peyman
[J]. SYNTHETIC COMMUNICATIONS, 2007, 37 (7-9) : 1097 - 1108
[5] Novel, efficient, and green procedure for the Knoevenagel condensation catalyzed by diammonium hydrogen phosphate in water
Balalaie, Saeed
Bararjanian, Morteza
Hekmat, Shohreh
Salehi, Peyman
[J]. SYNTHETIC COMMUNICATIONS, 2006, 36 (17) : 2549 - 2557
[6] Efficient synthesis of 1,4-disubstituted polyfunctional piperazines via a sequential one-pot Ugi/nucleophilic addition five-component reaction
Bararjanian, Morteza
Balalaie, Saeed
Movassagh, Barahman
Bijanzadeh, Hamid Reza
[J]. TETRAHEDRON LETTERS, 2010, 51 (25) : 3277 - 3279
[7] Six-Component Reactions for the Stereoselective Synthesis of 3-Arylidene-2-oxindoles via Sequential One-Pot Ugi/Heck Carbocyclization/Sonogashira/Nucleophilic Addition
Bararjanian, Morteza
Balalaie, Saeed
Rominger, Frank
Movassagh, Barahman
Bijanzadeh, Hamid Reza
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (09) : 2806 - 2812
[8] Enamine-based aldol organocatalysis in water: Are they really "all wet"?
Brogan, Andrew P.
Dickerson, Tobin J.
Janda, Kim D.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (48) : 8100 - 8102
[9] Water: Nature's Reaction Enforcer-Comparative Effects for Organic Synthesis "In-Water" and "On-Water"
Butler, Richard N.
Coyne, Anthony G.
[J]. CHEMICAL REVIEWS, 2010, 110 (10) : 6302 - 6337
[10] Chakraborti AK, 2007, GREEN CHEM, V9, P1335, DOI 10.1039/b710414f

← 1 2 3 4 5 →